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Bootlegger Compound Raided in Former Middletown Home of Oscar Hammerstein Sr.

On October 16, 1929, at the height of Prohibition, federal agents raided an isolated house atop the ridge in the Navesink section of Middletown, overlooking Sandy Hook Bay (pictured above…the person in the photo is unidentified). Before 1920, the house had been owned by the operatic and music hall impresario Oscar Hammerstein Sr. During the raid, agents found a powerful short-wave radio, a cellar full of sub-machine guns, automatic rifles, pistols and ammunition, and 16 men who denied any knowledge of the radio or weapons. The house was the center of a huge bootlegging operation smuggling rum from the Caribbean.

Press reports placed this house within the Hillside neighborhood of Atlantic Highlands. Four years later, it was front-page news when the smuggling ringleader Al Lillien was murdered there, and those press reports also placed the house within Atlantic Highlands.

As it turns out, the house had an Atlantic Highlands mailing address, presumably so as to avoid two different post offices having to deliver mail to the same street, but it was located on the Middletown side of the street.

The question often comes up, does this house still stand? And the answer is no. Not long after Lillien’s death it was turned into a home for boys, and then a nursing home which burned down in 1970.

Monmouth Timeline is grateful to the Monmouth County Clerk’s Archives offices and the Middletown Township Historic Society for helping to document the history of this property.


Boyd, Paul D.(2004). Atlantic Highlands: From Lenape Camps to Bayside Town. Arcadia Publishing, pp. 146-150.

The Day’s News in Pictures. (1929). The Courier News, Bridgewater, N.J., October 19, 1929, P. 14.

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